Stable hexylresorcinol compositions



United States Patent 3,274,057 STABLE HEXYLRESORCINOL COMPOSITIONS MaxA. Cherkas, Philadelphia, and Wayne M. Grim, Chalfont, Pa., assignors toMerck & Co., Inc., Rahway, N.J., a corporation of New Jersey No Drawing.Filed Oct. 30, 1963, Ser. No. 319,968 2 Claims. (Cl. 167-65) Thisinvention relates to a stabilized solution containing hexylresorcinol,such germicidal solutions demonstrating stability when administered inaerosol form.

Heretofore stability problems have been encountered when attempting toincorporate hexylresorcinol into an aerosol solution, arising in partbecause of the difiiculty of dissolving it in fluorinated hydrocarbonssuch as freons. A typical use of Freons in aerosol solutions isdescribed in Us. Patent No. 3,039,929, granted June 19, 1962, thedisclosure of which is hereby incorporated by reference and made a partof hereof. Such hexylresorcinol solutions when formed are rapidlydegraded, resulting in discoloration.

An object of this invention is to provide a stable solution capable ofbeing applied in aerosol form, which provides a mild anesthesia andanalgesia as well as germicidal efiectiveness at the site ofapplication.

It has been discovered in accordance with this invention thathexylresorcinol can be dissolved in a combination consisting essentiallyof anhydrous alcohol, trichloromonofluoromethane (Freon 11) and ascorbylpalmitate, thus producing a stable solution. It has further beendiscovered that the stable solution referred to above may beincorporated with Freons such as Freon 12 (dichloro difluoromethane) andFreon 114 (dichloro tetrafluoroethane) as a mixture, and may hemaintained for an indefinite period of time in a usual aerosolcontainer, and applied by spraying as a result of expansion of the dichlorodifluoromethane and dichlorotetrafluoroethane.

Specifically, the ingredients which are combined with hexylresorcinolfor the purpose of forming the stable solution are incorporated into thecomposition in the following proportions:

Percent by weight Hexylresorcinol 0.01 to 0.50 Anhydrous ethyl alcohol5.00 to 50.00 Trichloromonofluoromethane 15.00 to 60.00

Ascorbyl palmitate not greater than 0.03.

The solution prepared in accordance with the above disclosure is thenprepared for dispensing as an aerosol by addition of predeterminedquantities of dichlorodifuloromethane and dichlorotetrafluoroethane. Itis to be understood that other compatible pharmaceuticals and adjuvantscan be included in the above composition if desired.

It will further be understood that the ascorbyl palmitate is a necessaryingredient of the compositions in accordance with this invention, butthat it must be present in a preferred proportion no greater than about0.03% by weight, in. order to provide an effective stabilizer for thesystem.

The following specific examples are illustrative of preferredcompositions for carrying out this invention:

Freon l2/Freon 114, qs. (30-70 mixture), 100.00.

Freon 12/Freon 114, qs. (30-70 mixture), 100.00.

Example 4 Percent by weight Hexylresorcinol 0.50 Tyrothricin (defatted)0.02 Alcohol, anhydrous, SD38B 20.00 Freon 11 30.00 Ascorbyl palmitate0.03 Saccharin 0.06

Freon l2/Freon 114, qs. (30-70 mixture), 100.00.

Example 5 Percent by weight Hexylresorcinol 0.15 Tyrothricin (defatted)0.02 Alcohol, anhydrous, SD38B 15.00 Freon ll 35.00 Ascorbyl palmitate0.03 Saccharin 0.06

Freon IZ/Freon 114, qs. (30-70 mixture), 100.00.

The above examples of compositions produced in accordance with thisinvention are readily prepared by simply dissolving the hexylresorcinol,tyrothricin and anhydrous alcohol with the trichloromonofluoromethane atroom temperature, forming a clear solution. This solution is then mixedwith the ascorbyl palmitate and saccharin and placed in an aerosolcontainer. Following this, the dichlorodifluoromethane anddichlorotetrafluoroethane are incorporated into the aerosol containerunder pressure and the container is then sealed. When suitably mixed,the product is stable and may readily be applied in aerosol form.

Although this invention has been disclosed in connection with specificingredients in particular proportions, it will be appreciated thatequivalents may be substituted for specific compounds and that otherchanges maybe made all without departing from the spirit and scope ofthis invention as defined in the appended claims.

Having thus described our invention, we claim:

1. A stabilized germicidal composition suitable for administration as anaerosol consisting essentially of about 0.01 to 0.5% by weighthexylresorcinol, about 5 to by weight anhydrous ethanol, about 15 to byweight trichloromonofluoromethane, and a maximum of about 0.03% byweight ascorbyl palmitate.

2. A stabilized germicidal composition in aerosol form consistingessentially of the following ingredients in about the weight proportionsspecified:

Percent of weight Hexylresorcinol 0.10 Tyrothricin (defatted) 0.02Anhydrous ethanol, SD38B 30.00 Trichloromonofluoromethane 40.00 Ascorbylpalmitate 0.03

Saccharin 1- 0.06 Dichlorodifluoromethane and dichlorotetrafluoroethane,qs. 100.00.

4 References Cited by the Examiner UNITED STATES PATENTS 2,675,2934/1954 Baker 21--53 5 2,801,201 7/1957 Kipnis 167--58 3,039,929 6/1962Stanko 167--65 3,160,555 12/1964 Hamill et al 167-39 OTHER REFERENCESRegistered Trademark No. 426,346, Tyotocin (Sharpe 10 & Dohme),registered Dec. 24, 1946.

LEWIS GOTTS, Primary Examiner.

SHEP K. ROSE, Assistant Examiner.

1. A STABILIZED GERMICIDAL COMPOSITION SUITABLE FOR ADMINISTRATION AS ANAEROSOL CONSISTING ESSENTIALLY OF ABOUT 0.01 TO 0.5% BY WEIGHTHEXYLRESORCINOL, ABOUT 5 TO 50% BY WEIGHTT ANHYDROUS ETHANOL, ABOUT 15TO 60% BY WEIGHT TRICHLOROMONOFLUOROMETHANE, AND A MAXIMUM OF ABOUT0.03% BY WEIGHT ASCORBYL PALMITATE.